Sequential ene, Diels–Alder reactions of AF4-yne with 1,3,5-cycloheptatriene

(4,5-Dehydro)-1,1,2,2,9,9,10,10-octafluoro [2.2]paracyclophane (AF4-yne) undergoes an ene reaction with 1,3,5-cycloheptatriene, the adduct of which subsequently undergoes a further Diels–Alder reaction with a second equivalent of AF4-yne to give two stereoisomeric 2:1 adducts. A very small amount of the classic 1:1 Diels–Alder adduct also can be isolated from the reaction. Structure assignments of all products were determined by NMR through a series of H1–H1, H1–C13 one bond, and H1–C13 two and three bond correlation experiments as well as H1–H1 NOE experiments.

Graphical abstractAF4-yne undergoes sequential ene and Diels–Alder reactions to give two diastereoisomeric 2:1 adducts.Figure optionsDownload full-size imageDownload as PowerPoint slide